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CHEM 2380 - UNT > Chp. 11-13 Exam Review > Flashcards

Chp. 11-13 Exam Review Flashcards

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1
Q

What do you get when you oxidize secondary alcohol with PCC?

A

Ketone

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2
Q

What is Markovnikov’s Rule?

A

* “The rich get richer”

* The carbon with the largest # of carbon atoms gets the X (halogen) or OH bind to it

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3
Q

What is conjugation?

A

Sequence of alternating double or triple bonds.

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4
Q

What are 5 common nucleophiles?

A

I-

Br-

Cl-

HS-

H2S

RSH

HO-

RO-

NC-

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5
Q

What happens when secondary alcohol undergoes… a) KMnO4 b) H2CrO4 c) PCC

A

The secondary alcohol is converted to… a) Ketone b) Ketone c) Ketone

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6
Q

What is oxidation?

A
  1. Loss of electrons; 2. Adding an oxygen; 3. Adding an additional bond to the oxygen (eg. from single bonded oxygen, it becomes double bonded)
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7
Q

What are the names of the molecules from left to right?

A

Ketone; aldehyde; carbocyclic acid

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8
Q

What reagent can you use to convert an alkene to an epoxide?

A

MCPBA

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9
Q

What is chromic acid?

A

H2CrO4

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10
Q

What reagents can you use to reduce a ketone to a 2* alcohol?

A

NaBH4 or LAH

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11
Q

What product do you get when you apply PCC on a 1* alcohol?

A

Aldehyde

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12
Q

Are the following acids strong or weak? What are their pkas?

I-H

Br-H

Cl-H

SO3-H

HO3+

A

These are strong acids. Their pkas are…

I-H -11

Br-H -9

Cl-H -7

SO3-H -3

HO3+ -2

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13
Q

What product do you get?

A
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14
Q

What is this molecule?

A

Benzene

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15
Q

What do you get when you oxidize a 1* alcohol with H2CrO4?

A

Carboxylic Acid

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16
Q

What does aprotic mean?

A

The solvent does NOT have a proton on an electronegative atom.

17
Q

Are the following acids strong or weak? What are their pkas?

H20

1* alcohol

3* alcohol

NH3

A

These are weak acids. Their pkas are…

H20 15.7

1* alcohol 16

3* alcohol 18

NH3 38

18
Q

If the top row is a reactant, and the bottom row is the product, is this oxidation or reduction? Why?

A

Reduction. You are adding an H. (Gained electrons)

19
Q

What is the product if you use KMnO4, H2CrO4 or PCC with tertiary alcohol?

A

No Reaction

20
Q

What do you get when you oxidize primary alcohol with KMnO4?

A

Carboxylic Acid

21
Q

What product do you get if you reduce a carboxylic acid with NaBH4?

A

No Reaction

22
Q

What happens when primary alcohol undergoes… a) KMnO4 b) H2CrO4 c) PCC

A

The primary alcohol is converted to… a) Carboxylic acid b) Carboxylic acid c) Aldehyde

23
Q

Examples of polar aprotic solvents.

A

acetone, DMSO, DME and DMF

24
Q

When primary alcohol undergoes PCC, what happens?

A

It becomes an aldehyde.

25
Q

What are examples of reducing agents?

A

1) LiAlH4 (LAH);
2) NaBH4, H20;
3) H2, Ni;
4) Na, EtOH

26
Q

Is this oxidation or reduction?

What are the reagents to get the products from top to bottom?

A

This is oxidation.

KMnO4

H2CrO4

PCC

27
Q

What is a reduction?

A

Gain of electrons.

28
Q

What three reagents can you use to convert a 2* alcohol to a ketone?

A

KMnO4 and H2CrO4 and PCC

29
Q

Does strong Acid have a weak conjugate base?

A

True

30
Q

What happens when tertiary alcohol undergoes… a) KMnO4 b) H2CrO4 c) PCC

A

What happens when tertiary alcohol undergoes… a) No reaction b) No reaction c) No reaction

31
Q

What do you get when you reduce a carboxylic acid with LAH? How about with NaBH4?

A

1* alcohol; No Reaction

32
Q

What is the product from top to bottom?

A
33
Q

What mechanism is this? You have a tertiary, nucleophile, leaving group and a polar solven to stabilize the carbocation.

A

SN1

34
Q

This mechanism works for primary, maybe secondary; you need a strong nucleophile and leaving group; there is an inversion at the chirality center, need a polar solvent to dissolve nucleophile and it is favored by polar aprotic solvents.

A

SN2

35
Q

What is Hoffman Rule

A

* Elimination yields the least substituted alkene

* use a bulky base such as tert-butoxide (t-BuOK) in tert-butyl alcohol (t-buOH).

36
Q

* Favors substrates that can form stable carbocations.

* Bulky group

*Alcohols dehydrated follows this mechanism in 2* and 3* alcohols

* Favored by use of POOR NUCLEOPHILES (weak bases)

A

E1

37
Q

* Uses a 2* or 3* alkyl halide is possible;

* HIgh temperature favors elimination over substitution

* Use EtONA/EtOH and t-BuOK/t-BuOH

Zaitsev product

* Primary alcohols follow this mechanism or rearrangement

* H must be anti to leaving group

A

E2

38
Q
A

CHEM 2380 - UNT (1 decks)

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